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Re: New Engine vs. Rebuilt Engine
Early Windstars were noted for head gasket and transmission problems (specifically the '95 and '96 model years). I believe all of these serious problems were resolved before the '99 models.
I've had no transmission problems in my '00 - but I also do some trailer towing, so I'm more interested in the details than most folks. My interest in the '02+ models is because those transmission internals are shared with the F150. Again, this isn't a knock on post '96-or-so transmissions.
You should do fine with a well-cared-for '99.
Regarding other makes: Note that Chrysler went through their own years of transmission horror stories - though, again, by the late 90's these problems seemed to be a thing of the past. Personally, I like the Windstar design - and the fact that you get a lot for your money compared to other choices.
As always: Do your research; weigh your choices; make your decision.
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2000 Windstar LX 3.8
1995 Contour GL 2.5
1986 Mustang GT 5.0 --> Sold, but missed on sunny days
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